• Alternate Text

  • Loading

  • Omazing Gift Guide
  • Podcast
  • Baldwin Park Living
  • Calendars
  • Public Notices
  • e-Newspaper App
  • Subscribe
  • West Orange Times
    • News
    • Opinion
    • Neighborhood
    • Sports
    • Business
    • Real Estate
    • Obituaries
    • Your Town
    • Health
    • History
    • House Wise
    • Hurricane
  • Southwest Orange
    • News
    • Opinion
    • Neighborhood
    • Real Estate
    • Sports
    • Business
    • Obituaries
    • Your Town
    • Health
    • History
    • House Wise
    • Hurricane
  • School Zone
    • Graduation 2025
  • Sports
    • Friday Night Sights
    • High School
    • Athlete of the Week
    • Youth Sports
    • Game Film
  • Arts & Entertainment
    • Season Magazine
    • Things to Do
    • Eat + Drink
    • Arts & Culture
    • Foodie Call
    • Summer Fun Guide
  • Galleries
  • Special Sections
  • West Orange Times
    • West Orange Times
    • News
    • Opinion
    • Neighborhood
    • Sports
    • Business
    • Real Estate
    • Obituaries
    • Your Town
    • Health
    • History
    • House Wise
    • Hurricane
  • Southwest Orange
    • Southwest Orange
    • News
    • Opinion
    • Neighborhood
    • Real Estate
    • Sports
    • Business
    • Obituaries
    • Your Town
    • Health
    • History
    • House Wise
    • Hurricane
  • School Zone
    • School Zone
    • Graduation 2025
  • Sports
    • Sports
    • Friday Night Sights
    • High School
    • Athlete of the Week
    • Youth Sports
    • Game Film
  • Arts & Entertainment
    • Arts & Entertainment
    • Season Magazine
    • Things to Do
    • Eat + Drink
    • Arts & Culture
    • Foodie Call
    • Summer Fun Guide
  • Galleries
  • Special Sections
  • West Orange On The Go
  • Omazing Gift Guide
  • Podcast
  • Baldwin Park Living
  • Calendars
  • Public Notices
  • Subscribe

Arts + Entertainment

  • By Observer Staff
  • May 6, 2026
Winter Garden Heritage Foundation to host Heritage Happy Hour

The event will take place from 5 to 7:30 p.m. Wednesday, May 13, at Heller Hall, 21 E. Plant St., Winter Garden.

  • Arts + Entertainment
  • Things to Do
  • By Observer Staff
  • May 6, 2026
Opera Orlando celebrates end of 10th season with concert

This one-night-only concert will have you singing along with selections from Rigoletto, The Magic Flute, La Traviata, Carousel, Les Miserables, and much, much more.

  • Arts + Entertainment
  • Things to Do
  • By Observer Staff
  • May 6, 2026
Hamlin saddles up for 2026 Hoedown

The Hamlin Hoedown will take place from 10 a.m. to 2 p.m. Saturday, May 16, in the Hamlin Green Space, 14111 Shoreside Way, Winter Garden.

  • Arts + Entertainment
  • Things to Do
  • By Observer Staff
  • May 6, 2026
Treat your mom to a Wine Walk this weekend

This event will take place from 5:30 to 7:30 p.m. Saturday, May 9, at Southern Hill Farms, 16651 Schofield Road, Clermont.

  • Arts + Entertainment
  • Things to Do
  • By Observer Staff
  • May 6, 2026
FIT 407 to jumpstart Mother’s Day weekend with pop-up event

The event takes place from 8:30 a.m. to 1 p.m. Saturday, May 9, at Fit 407, 16406 New Independence Parkway, Winter Garden.

  • Arts + Entertainment
  • Things to Do
  • By Observer Staff
  • May 6, 2026
Latin-themed fiesta will heat up Flamingo Crossings

The event takes place from 6 to 9 p.m. Friday, May 8, at Flamingo Crossings in Horizon West.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • April 29, 2026
Winter Garden VFW saddles up for Derby Day

The event will take place from 5 to 9 p.m. Saturday, May 2, at the post, 1170 E. Plant St., Winter Garden.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • April 29, 2026
Ocoee plans Cinco de Mayo fiesta

The city’s Cinco De Mayo Block Party takes place from 6 to 9 p.m. Friday, May 1, in downtown Ocoee.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • April 29, 2026
Shop ’til you drop this weekend in Winter Garden

Downtown Winter Garden will host its Shop, Dine and Stroll event from 9 a.m. to 10 p.m. Saturday, May 2, in downtown Winter Garden.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • April 29, 2026
Arts at the J to boogie with AARP Orlando Salsa Celebration

This event takes place from 2 to 4:30 p.m. Sunday, May 3, at the Pargh Event Center at the Rosen JCC, 11184 S. Apopka-Vineland Road, Orlando.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • April 29, 2026
Ocoee Police to serve up annual picnic

This event will take place from 11 a.m. to 2 p.m. Saturday, May 2, at Vignetti Park, 1910 Adair St., Ocoee.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • April 29, 2026
West Orange Junior Service League rides with annual Run of the Roses

This year’s event will take place from 5 to 10 p.m. Saturday, May 2, at Clermont Arts and Recreation Center, 3700 S. U.S. 27, Clermont.

  • Arts + Entertainment
  • Things to Do
    By
  • Leticia Silva
  • April 27, 2026
West Orange High to present 'Newsies'

Performances will take place from Thursday, April 30, to Sunday, May 3, at 1625 Beulah Road, Winter Garden.

  • Observer School Zone
  • News
    By
  • Michael Eng
  • April 23, 2026
Rosen JCC to present Israel North to South

The event takes place from 3:30 to 6:30 p.m. Sunday, April 26, at the Rosen JCC, 11184 S. Apopka-Vineland Road, Orlando.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • April 23, 2026
Horizon West residents: Street party set for Friday

The Family Friday Street Party will take place from 5 to 8 p.m. Friday, April 24, at The Mark, 9250 Miley Drive, Winter Garden.

  • Arts + Entertainment
  • Things to Do
1 2 3 4 5 »

Newsletter

Sign up to receive our news in your inbox!
Click to Sign Up

Latest News Arts + Entertainment

1
  • May 7, 2026
Winter Garden seeks input on Comprehensive Plan update
2
  • May 7, 2026
Oakland schedules Spring Clean Up days
3
  • May 7, 2026
Two Southwest Orange Orlando Health hospitals earn 'A'
4
  • May 6, 2026
Chain of Lakes Animal Clinic partners with domestic violence shelter
5
  • May 6, 2026
Lane closures in Windermere to last a week for road repairs

Contact

  • 210 S. Dillard St.,
  • Winter Garden, FL 34787
  • Phone: 407-656-2121
  • Email: [email protected]

sister sites

  • Business Observer
  • Jax Daily Record
  • Observer Local News
  • Your Observer

  • e-Newspaper App

more

  • About Us
  • Contact Us
  • Advertise
  • Subscribe
  • School Fundraiser
  • Jobs
  • Rack Locations
  • Sponsorships
  • Privacy Policy

Newsletter

Sign up to receive our news in your inbox!

Click to Sign Up

Verified Audit

  • USPS Periodicals Permit
  • USPS# 687-120
  • as required for Public Notices per F.S. 50.011
  • Statement of Ownership
  • Copyright © 2026 Observer Media Group Inc., All Rights Reserved